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Sodium channel blockers

A substituted and unsubstituted technology, applied in the field of sodium channel blockers, can solve problems such as sedation problems

Active Publication Date: 2017-08-29
IN THERAPEUTICS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This drug is generally safe, but can be problematic in high doses with regard to sedation

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0438] Example 1) Preparation of (5-chloro-4-(5-chloro-3-methyl-1H-indazol-1-yl)-2-fluoro-N-(methylsulfonyl)benzamide

[0439]

[0440] Dissolve 0.2g (1.2mmol) of 5-chloro-3-methyl-1H-indazole in 10mL of anhydrous N,N-dimethylformamide, add 0.78g (2.4mmol) of cesium carbonate and 0.32g (1.2 mmol) 5-Chloro-2,4-difluoro-N-(methylsulfonyl)benzamide. The reaction mixture was stirred at 150 °C for 1 hour, the organic layer was separated, treated with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was separated by column chromatography to obtain 0.15 g (yield: 30%) of the title compound.

[0441] 1H NMR (MeOD) δ: 7.84 (s, 1H), 7.82-7.81 (d, 1H), 7.45-7.43 (d, 2H), 7.30-7.28 (d, 1H), 3.30 (s, 3H), 2.60 ( s, 3H).

Embodiment 6

[0442] Example 6) Preparation of 4-(3-acetylamino-5-chloro-1H-indazol-1-yl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide

[0443]

[0444] Dissolve 0.1g (0.24mmol) of 4-(3-amino-5-chloro-1H-indazol-1-yl)-5-chloro-2-fluoro-N-(methylsulfonyl)benzamide in 5mL without In water tetrahydrofuran, 0.018 g (0.24 mmol) of acetyl chloride was added thereto. The reaction mixture was stirred at room temperature for 2 hours, the organic layer was separated, treated with magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was separated by column chromatography to obtain 0.033 g (yield: 30%) of the title compound.

[0445] 1H NMR (MeOD) δ: 7.80-7.99(d, 1H), 7.64-7.62(d, 1H), 7.40-7.38(d, 1H), 7.28-7.27(d, 2H), 3.15(s, 3H), 2.25(s, 3H).

Embodiment 24

[0446] Example 24) Preparation of 5-chloro-4-(3-chloro-5-cyclopropyl-1H-indazol-1-yl)-2-fluoro-N-(methylsulfonyl)benzamide

[0447]

[0448] Under nitrogen, 25 mL of tetrahydrofuran was added to 1.0 g (7.0 mmol) of zinc(II) chloride, and 4.0 mL (7.0 mmol, 1.7 M of tetrahydrofuran) of cyclopropylmagnesium bromide was added thereto, followed by stirring at room temperature for 30 min . Under nitrogen, the reaction mixture was added to 0.4 g (1.72 mmol) of 5-bromo-3-chloro-1H-indazole, and then reacted at 100° C. for 10 minutes using a microwave reactor. The organic layer was separated and concentrated under reduced pressure. The residue was separated by column chromatography to obtain 0.24 g (yield: 80%) of 3-chloro-5-cyclopropyl-1H-indazole.

[0449] 1H NMR (MeOD) δ: 7.36 (d, 1H), 7.29 (s, 1H), 7.18 (d, 1H), 2.00 (m, 1H), 0.95 (d, 2H), 0.68 (d, 2H).

[0450] 0.10 g (yield: 18%) of the title compound were prepared in the same manner as described in Example 1, except that 3...

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PUM

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Abstract

The present invention relates to a compound having a blocking effect against sodium ion channels, particularly Nav 1.7, a preparation method thereof and use thereof. The compound represented by the Formula 1 or a pharmaceutically acceptable salt, hydrate, solvate or isomer thereof can be effectively used in the prevention or treatment of pains, for example, acute pain, chronic pain, pain from nervous disease, postoperative pain, migraine, arthralgia, neuropathy, nerve injury, diabetic neuropathy, neuropathic disease, epilepsy, arrhythmia, myotonia, ataxia, multiple sclerosis, irritable bowel syndrome, urinary incontinence, visceral pain, depression, erythromelalgia, paroxysmal extreme pain disorder (PEPD).

Description

technical field [0001] The invention relates to a compound capable of blocking sodium ion channels, especially Nav1.7, its preparation method and its use. Background technique [0002] Voltage-gated sodium channels are found in all excitable cells, including muscle cells and nerve cells of the central and peripheral nervous systems. These sodium channels are critical for the initiation and propagation of electrical signals in the nervous system. Thus, sodium channels are in place and their proper function is crucial for the proper function of the nerve. Ultimately, abnormal Nav channels play a decisive role in various diseases such as epilepsy, cardiac arrhythmia, myotonia, ataxia, multiple sclerosis, irritable bowel syndrome, urinary incontinence, visceral pain, depression and pain. Currently, ten Nav channels (Nav 1.1-1.9, Nax) have been reported in humans. Among them, four channels, Nav1.3, Nav1.7, Nav1.8 and Nav1.9, are known to be closely related to the transmission ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/54C07D231/56A61K31/416
CPCC07D231/56C07D403/12C07D401/04C07D401/06C07D403/04C07D403/10C07D417/04C07D417/12C07D417/14C07D471/04C07D209/10C07D209/30C07D209/42C07D401/12A61P1/04A61P13/02A61P17/02A61P19/02A61P21/00A61P21/02A61P25/00A61P25/04A61P25/06A61P25/08A61P25/18A61P25/24A61P43/00A61P9/06A61P3/10A61K31/416
Inventor 金知德李炯根金仁宇全善娥郑名淇金孝信
Owner IN THERAPEUTICS CO LTD
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